Hydrogen bonding in aromatic polyamine 2-guanidinobenzimidazole: Study based on density functional theory calculations

The role of inter- and intramolecular hydrogen bonding is very important for defining the reactivity of a great diversity of structures. In aromatic nucleophilic substitutions (SNAr) with amines in aprotic solvents, the attendance of hydrogen bond interactions (solute-solute and solute-solvent) has...

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Detalles Bibliográficos
Autores principales:	Bergero, F., Alvaro, C.E.S., Nudelman, N.S., Ramos de Debiaggi, S.
Formato:	JOUR
Materias:	2-Guanidinobenzimidazole Ab-initio calculations Aromatic nucleophilic substitution Hydrogen bonded nucleophiles Mixed-aggregates
Acceso en línea:	http://hdl.handle.net/20.500.12110/paper_01661280_v896_n1-3_p18_Bergero
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

id	todo:paper_01661280_v896_n1-3_p18_Bergero
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spelling	todo:paper_01661280_v896_n1-3_p18_Bergero2023-10-03T15:03:33Z Hydrogen bonding in aromatic polyamine 2-guanidinobenzimidazole: Study based on density functional theory calculations Bergero, F. Alvaro, C.E.S. Nudelman, N.S. Ramos de Debiaggi, S. 2-Guanidinobenzimidazole Ab-initio calculations Aromatic nucleophilic substitution Hydrogen bonded nucleophiles Mixed-aggregates The role of inter- and intramolecular hydrogen bonding is very important for defining the reactivity of a great diversity of structures. In aromatic nucleophilic substitutions (SNAr) with amines in aprotic solvents, the attendance of hydrogen bond interactions (solute-solute and solute-solvent) has been proposed to understand kinetic results. In order to hold up recently reported experimental results on SNAr, in this paper we study structural and electronic properties of the aromatic polyamine 2-guanidinobenzimidazole, the aprotic polar solvent molecule dimethylsulphoxide and their interactions. Semi-empirical and ab-initio density functional theory calculations were performed to investigate, in particular, the possibility of hydrogen bond formation. It is found that 2-guanidinobenzimidazole presents intra- and intermolecular hydrogen bond formation leading to homo 2-GB and mixed solute-solvent dimers; being the latter energetically slightly more favorable than the former one. © 2008 Elsevier B.V. All rights reserved. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_01661280_v896_n1-3_p18_Bergero
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	2-Guanidinobenzimidazole Ab-initio calculations Aromatic nucleophilic substitution Hydrogen bonded nucleophiles Mixed-aggregates
spellingShingle	2-Guanidinobenzimidazole Ab-initio calculations Aromatic nucleophilic substitution Hydrogen bonded nucleophiles Mixed-aggregates Bergero, F. Alvaro, C.E.S. Nudelman, N.S. Ramos de Debiaggi, S. Hydrogen bonding in aromatic polyamine 2-guanidinobenzimidazole: Study based on density functional theory calculations
topic_facet	2-Guanidinobenzimidazole Ab-initio calculations Aromatic nucleophilic substitution Hydrogen bonded nucleophiles Mixed-aggregates
description	The role of inter- and intramolecular hydrogen bonding is very important for defining the reactivity of a great diversity of structures. In aromatic nucleophilic substitutions (SNAr) with amines in aprotic solvents, the attendance of hydrogen bond interactions (solute-solute and solute-solvent) has been proposed to understand kinetic results. In order to hold up recently reported experimental results on SNAr, in this paper we study structural and electronic properties of the aromatic polyamine 2-guanidinobenzimidazole, the aprotic polar solvent molecule dimethylsulphoxide and their interactions. Semi-empirical and ab-initio density functional theory calculations were performed to investigate, in particular, the possibility of hydrogen bond formation. It is found that 2-guanidinobenzimidazole presents intra- and intermolecular hydrogen bond formation leading to homo 2-GB and mixed solute-solvent dimers; being the latter energetically slightly more favorable than the former one. © 2008 Elsevier B.V. All rights reserved.
format	JOUR
author	Bergero, F. Alvaro, C.E.S. Nudelman, N.S. Ramos de Debiaggi, S.
author_facet	Bergero, F. Alvaro, C.E.S. Nudelman, N.S. Ramos de Debiaggi, S.
author_sort	Bergero, F.
title	Hydrogen bonding in aromatic polyamine 2-guanidinobenzimidazole: Study based on density functional theory calculations
title_short	Hydrogen bonding in aromatic polyamine 2-guanidinobenzimidazole: Study based on density functional theory calculations
title_full	Hydrogen bonding in aromatic polyamine 2-guanidinobenzimidazole: Study based on density functional theory calculations
title_fullStr	Hydrogen bonding in aromatic polyamine 2-guanidinobenzimidazole: Study based on density functional theory calculations
title_full_unstemmed	Hydrogen bonding in aromatic polyamine 2-guanidinobenzimidazole: Study based on density functional theory calculations
title_sort	hydrogen bonding in aromatic polyamine 2-guanidinobenzimidazole: study based on density functional theory calculations
url	http://hdl.handle.net/20.500.12110/paper_01661280_v896_n1-3_p18_Bergero
work_keys_str_mv	AT bergerof hydrogenbondinginaromaticpolyamine2guanidinobenzimidazolestudybasedondensityfunctionaltheorycalculations AT alvaroces hydrogenbondinginaromaticpolyamine2guanidinobenzimidazolestudybasedondensityfunctionaltheorycalculations AT nudelmanns hydrogenbondinginaromaticpolyamine2guanidinobenzimidazolestudybasedondensityfunctionaltheorycalculations AT ramosdedebiaggis hydrogenbondinginaromaticpolyamine2guanidinobenzimidazolestudybasedondensityfunctionaltheorycalculations
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Hydrogen bonding in aromatic polyamine 2-guanidinobenzimidazole: Study based on density functional theory calculations

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